1,2-Dichloroethane → N-(t-butoxycarbonyl)-L-homophenylalaninamide

HRID 396580ノート

反応式

HRID 396580 の反応式
[NH4+:1].[OH-:2].[C:3]([O:7][C:8]([NH:10][C@H:11](C(O)=O)[CH2:12][CH2:13][C:14]1C=CC=CC=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(Cl)CCl.[CH:27]1[CH:28]=[CH:29][C:30]2N(O)N=N[C:31]=2[CH:32]=1>CN(C=O)C.C(Cl)Cl>[C:3]([O:7][C:8]([NH:10][C:11](=[O:2])[C@H:12]([CH2:13][CH2:14][C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:32]=1)[NH2:1])=[O:9])([CH3:6])([CH3:5])[CH3:4]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

生成物 1

HCID 21339350N-(t-butoxycarbonyl)-L-homophenylalaninamide収率 78%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

NH4OH (4 mL) was added to a premixed (15 min) solution of N-(t-butoxycarbonyl)-L-homophenylalanine (4.00 g, 14.3 mmol), EDC (3.24 g, 17.2 mmol), and HOBT (2.32 g, 17.2 mmol) in DMF (20 mL) at room temperature. After 16 h the reaction mixture was diluted with CH2Cl2 and filtered, washed sequentially with 10% aqueous HCI, satd. NaHCO3, H2O (×3), brine, dried over Na2SO4, and concentrated giving N-(t-butoxycarbonyl)-L-homophenylalaninamide (3.10 g, 78%) as a white solid.

後処理

  1. filtrationfiltered
  2. washwashed sequentially with 10% aqueous HCI
  3. dry with materialNaHCO3, H2O (×3), brine, dried over Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-2af8ac02096b49868fb99442e48401a3
出典データセット
uspto-grants-2003_08
特許番号
US06608057B2

反応ノート

読み込み中…